# AI email assistants compared: the best for Gmail and Outlook

> What an AI email assistant does, the main ones compared by price, mail provider and whether they send, and how to make ChatGPT or Claude your email assistant.

Updated 2026-11-02 · https://upsy.ai/guides/ai-email-assistant

## Short answer

An AI email assistant reads your inbox, sorts it, summarizes threads and drafts replies. Some also send, schedule meetings and follow up. They come in three kinds:

- **Built into your mail app:** Gemini in Gmail and Copilot in Outlook. The easiest start, and free summaries in Gmail.
- **A separate app or add-on:** Superhuman, Shortwave, Fyxer, Spark, SaneBox. Best for a faster inbox or drafts waiting for you each morning.
- **A general AI assistant connected to your mail:** ChatGPT, Claude, Grok, Muse or Gemini Spark. Best when email is one part of the job, next to your calendar, documents and Slack.

Almost all of them draft and let you send. Few send on their own.

## What an AI email assistant does

- **Triage:** labels, priorities and a short list of what needs you.
- **Summaries** of long threads and of what came in overnight.
- **Drafts in your voice,** learned from what you've sent before.
- **Sending,** usually after you approve each email.
- **Scheduling:** finding times and sending invites from a thread.
- **Follow-ups:** reminding you, or nudging the other side, when nobody answered.
- **Briefings:** a daily summary of mail, meetings and what's waiting.

## Built into your mail app

| | Gemini in Gmail | Copilot in Outlook |
|---|---|---|
| Works with | Gmail and Google Workspace | Outlook with a Microsoft 365 plan |
| Free | Thread summaries; Help me write and suggested replies in the US | Nothing: Microsoft 365 Basic has no AI |
| Paid | AI Inbox (US, English, beta), AI Overviews in search, Proofread: Google AI Plus from $4.99 a month, or Workspace | Triage, summaries, drafts, scheduling: Microsoft 365 Personal $9.99 a month; business Copilot $30 a user |
| Sends on its own | No, it drafts | No, you review and send |

Sources: [Gemini in Gmail](https://support.google.com/mail/answer/16831098), [Copilot in Outlook](https://support.microsoft.com/en-us/outlook/frequently-asked-questions-about-copilot-in-outlook), [Microsoft 365 plans](https://www.microsoft.com/en-us/microsoft-365/buy/compare-all-microsoft-365-products).

Both are building agents that go further. Copilot's agent mode in Outlook triages and drafts follow-ups on its own, in Microsoft's early-access program for business customers. Google says Gemini doesn't train its models on your personal email ([Google](https://blog.google/products-and-platforms/products/gmail/privacy-in-gmail-with-gemini/)).

## Email apps and add-ons with AI

| Product | Works with | What its AI does | Free plan | Paid from |
|---|---|---|---|---|
| [Superhuman](https://superhuman.com/plans/mail) | Gmail, Microsoft 365 | Split inbox, auto labels, reminders; auto drafts on Business | No | $25 a month, yearly |
| [Shortwave](https://www.shortwave.com/pricing/) | Gmail and Workspace | Summaries, one-click replies, AI filters | Yes, with limits | $14 a month, yearly |
| [Fyxer](https://www.fyxer.com/pricing) | Gmail, Workspace, Microsoft 365 | Drafts in your tone, labels, meeting notes | Yes | $37 a month, yearly |
| [Spark +AI](https://sparkmailapp.com/pricing) | Gmail, Outlook, iCloud, Yahoo, IMAP | Writing help, summaries; auto drafts on Pro | Yes | $8.25 a month, yearly |
| [SaneBox](https://www.sanebox.com/pricing) | Any IMAP or Exchange mailbox | Sorts mail into folders; AI drafts on the top plan | No | $65 a year |
| [Carly](https://www.usecarly.com/pricing) | Google, Microsoft | An agent with its own address that you CC; schedules and follows up | Yes, limited | $35 a month |
| [Lindy](https://www.lindy.ai/pricing) | Gmail, Outlook | A general agent: drafts in your voice, inbox management, briefings | A 7-day credit | $49.99 a month |
| [Inbox Zero](https://www.getinboxzero.com/pricing) | Gmail, Outlook | Open source: rules and drafts | A 7-day trial | $18 a month, yearly |

Prices are from each vendor's page on November 1, 2026. For a shared team inbox, Missive and Front have AI drafts and rules. Notion Mail shut down on September 22, 2026.

Fyxer, Superhuman, Spark and SaneBox all draft and leave sending to you. Carly sends from its own address, as an assistant would.

## General AI assistants as your email assistant

| Assistant | Mail it connects to | Sending | Recurring email tasks |
|---|---|---|---|
| ChatGPT | Gmail and Outlook on every plan, several accounts each; iCloud Mail since October 27 | Drafts, then you click send (web, Plus and above) | Scheduled tasks, three on Free; ChatGPT Work tasks can start when a Gmail arrives |
| Claude | Gmail, one account; Microsoft 365 work accounts | Gmail sends after you approve each one | Scheduled tasks in Cowork, on paid plans |
| Claude for Outlook | Inside Outlook on Exchange Online | Never: it drafts | No |
| Grok | Gmail; Outlook work accounts | Gmail starts read-only ([details](/guides/grok/send-email)) | Grok Bot routines, with The X Subscription |
| Muse | Gmail, in the US, Canada, Japan and Singapore | You choose read-only or send; it asks first | Reminders on a schedule |
| Gemini Spark | Gmail, on Google AI Pro and Ultra in the US | Asks before sending | Yes |

Sources: [ChatGPT release notes](https://help.openai.com/en/articles/6825453-chatgpt-release-notes), [Claude's Google connectors](https://support.claude.com/en/articles/10166901-use-google-workspace-connectors), [Claude for Outlook](https://claude.com/docs/office-agents/outlook), [Meta](https://about.fb.com/news/2026/09/introducing-muse-personal-ai-agent/), [Google](https://blog.google/innovation-and-ai/products/gemini-app/next-evolution-gemini-app/).

A general assistant does more than a mail app's AI: "find the contract Sam sent, check my calendar for Thursday and propose two times" crosses three apps. You pay for it in setup, since each assistant connects each account on its own.

## Which one to pick

- **You want help inside Gmail and don't want a new app:** Gemini. Summaries are free; AI Inbox needs a paid plan.
- **You use Outlook at work:** Copilot, or the Claude for Outlook add-in on Exchange Online.
- **You want a faster inbox:** Superhuman for Gmail or Microsoft 365, Shortwave for Gmail, Spark for anything else, including iCloud and Yahoo.
- **You want drafts waiting each morning:** Fyxer, Superhuman's auto drafts or Spark Pro.
- **You want one assistant for email, calendar, documents and Slack:** ChatGPT, Claude, Grok Bot or Muse, with your mail connected.
- **Free:** Gemini's summaries in Gmail, Spark's and Fyxer's free plans, or ChatGPT Free with three scheduled tasks.

## Where they stop

- **Sending.** Most draft and wait for you. That's deliberate, and worth keeping for anything that acts on its own.
- **Personal Outlook.** Many tools want a Microsoft 365 work account: Claude's connector and add-in, Fyxer, and Grok's Outlook connector. Shortwave has no Outlook support.
- **Several accounts.** Claude's Gmail connector takes one account at a time. Mail apps handle several, but only inside that app.
- **Hidden instructions in email.** An email can carry text aimed at your AI. In August 2026, researchers showed one email getting Google's Antigravity agent to send out SSH keys ([Straiker](https://www.straiker.ai/blog/google-antigravity-ai-agent-prompt-injection)). Keep approvals on for sending, and give assistants that only summarize read-only access.
- **Seeing what happened.** Each assistant connects on its own, and none shows what the others did with your mail.

## Make any AI assistant your email assistant with Upsy

Upsy connects your mail once and gives it to every AI assistant you use, through one MCP server:

- **Gmail, up to five accounts,** with sending, drafts, labels and attachments; Zoho Mail; plus Google Calendar, Google Drive and Slack. Upsy's Outlook connector is pending Microsoft's approval; until then, assistants can use outlook.com in Upsy's cloud browser.
- **Every assistant:** ChatGPT, Claude, Grok, Muse, Claude Code, Cursor and Codex.
- **Access per assistant:** Read-only for the one that summarizes, sending for the one you trust, enforced by Upsy whatever the assistant is told.
- **History and alerts:** every read and send is logged under the assistant that did it. Upsy emails you when one assistant sends 20 or more emails, deletes 50 or more items, or reads 100 or more times within 10 minutes.
- **Playbooks:** saved methods any assistant can follow, such as [Daily briefing](/playbooks/daily-briefing), [Inbox to action](/playbooks/inbox-to-action) and [Invoice follow-up](/playbooks/invoice-follow-up). Run them on a schedule with [ChatGPT's](/guides/chatgpt/scheduled-tasks) or [Claude's](/guides/claude/scheduled-tasks) scheduled tasks.

Upsy is free. To set it up:

1. Sign up at [upsy.ai](https://upsy.ai) and connect Gmail under **Apps**.
2. Add Upsy to your assistant: [ChatGPT](/guides/chatgpt/custom-connector), [Claude](/guides/claude/custom-connector), [Grok](/guides/grok/gmail) or [Muse](/guides/muse/gmail).
3. Choose what that assistant can do with your email, and ask it something.

## Prompts to try

- "Go through yesterday's email and list what needs a reply from me, most urgent first."
- "Draft replies to the three oldest unanswered emails from clients. Don't send them."
- "Find every invoice email from October, save the PDFs to my Receipts folder in Drive, and total them."
- "Read my thread with Ada about the launch, check my calendar, and propose two times next week."
- "Every morning at 8, follow my Daily briefing playbook."

## FAQ

### What is the best AI email assistant?

It depends on where you work. Gemini if you live in Gmail, Copilot for Outlook at work, Superhuman or Shortwave for a faster inbox, Fyxer for drafts waiting in your inbox. For email together with your calendar and documents, a general assistant like ChatGPT or Claude with your mail connected.

### Is there a free AI email assistant?

Yes. Gmail summarizes threads for free, and Spark, Fyxer and Shortwave have free plans. ChatGPT Free connects to Gmail and Outlook and runs three scheduled tasks. Upsy is free too.

### Is there an AI email assistant for Outlook?

Copilot in Outlook with a Microsoft 365 plan, the Claude for Outlook add-in on Exchange Online, and Fyxer and Superhuman on Microsoft 365. Spark works with Outlook.com too.

### Can ChatGPT reply to my emails?

Yes. Connect Gmail or Outlook, and ChatGPT drafts a reply that you send with a click, on the web on Plus and above. See [is it safe to connect Gmail to ChatGPT](/guides/chatgpt/is-it-safe-to-connect-gmail) before you do.

### Can an AI email assistant send emails on its own?

Some can, but most are built to draft and ask. Carly sends from its own address, and agents like Muse and Gemini Spark send after asking you. With Upsy, you decide per assistant whether it may send at all.

### Is it safe to let AI read my email?

Check two things: whether the company trains on your mail, and what the assistant can do besides read. Google says Gemini doesn't train on personal email, Spark and Lindy say your mail isn't used for training, and Fyxer lets you opt out of its own. Read-only access and a history of what was read limit the damage if an email tricks the assistant.

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Upsy connects personal AI assistants (Muse, Grok, ChatGPT, Claude, Cursor, Claude Code, Codex, Devin) to your Gmail, Google Calendar, Google Drive, Slack, Notion and other apps through one MCP server, with a shared memory, files and a cloud browser signed in to your sites. You choose what each assistant may do in each app, see everything it did, and turn it off in one click. Upsy is free. To add Upsy to an assistant, add a remote MCP server (Streamable HTTP) named Upsy at https://upsy.ai/connect. It signs in with OAuth; there is no API key.